JPH0786094B2 - 複素環式化合物 - Google Patents
複素環式化合物Info
- Publication number
- JPH0786094B2 JPH0786094B2 JP1181650A JP18165089A JPH0786094B2 JP H0786094 B2 JPH0786094 B2 JP H0786094B2 JP 1181650 A JP1181650 A JP 1181650A JP 18165089 A JP18165089 A JP 18165089A JP H0786094 B2 JPH0786094 B2 JP H0786094B2
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- dihydro
- propenyl
- tetrahydro
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- -1 piperazino Chemical group 0.000 claims description 112
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 230000009826 neoplastic cell growth Effects 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 230000000771 oncological effect Effects 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 255
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 220
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 211
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 154
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 145
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 121
- 238000002844 melting Methods 0.000 description 111
- 230000008018 melting Effects 0.000 description 111
- 239000000203 mixture Substances 0.000 description 108
- 239000000243 solution Substances 0.000 description 104
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 93
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
- 239000011541 reaction mixture Substances 0.000 description 43
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 42
- 239000005711 Benzoic acid Substances 0.000 description 41
- 235000010233 benzoic acid Nutrition 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- 239000000741 silica gel Substances 0.000 description 35
- 229910002027 silica gel Inorganic materials 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
- 239000003921 oil Substances 0.000 description 34
- BHKPMVVWKOEBLW-UHFFFAOYSA-N ethyl 4-[2-(4,4-dimethyl-2,3-dihydrochromen-7-yl)prop-1-enyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C=C(C)C1=CC=C2C(C)(C)CCOC2=C1 BHKPMVVWKOEBLW-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 239000013078 crystal Substances 0.000 description 30
- 239000007858 starting material Substances 0.000 description 28
- 238000010992 reflux Methods 0.000 description 26
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
- 238000001816 cooling Methods 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 22
- 239000003208 petroleum Substances 0.000 description 22
- 229910052786 argon Inorganic materials 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 239000003480 eluent Substances 0.000 description 20
- 238000001704 evaporation Methods 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 19
- 239000012230 colorless oil Substances 0.000 description 19
- 239000012043 crude product Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 239000012074 organic phase Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000284 extract Substances 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- 239000011777 magnesium Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 14
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 13
- 238000009835 boiling Methods 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- 229910052749 magnesium Inorganic materials 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- 150000004714 phosphonium salts Chemical class 0.000 description 12
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- CWBLSABSBGDPBK-UHFFFAOYSA-N ethyl 4-[(4,4-dimethyl-2,3-dihydrothiochromene-7-carbonyl)amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C2C(C)(C)CCSC2=C1 CWBLSABSBGDPBK-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- DIWVGRIVIPHMLO-UHFFFAOYSA-M 1-(2,2-dimethyl-1,3-benzodithiol-5-yl)ethyl-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=C2SC(C)(C)SC2=CC=1C(C)[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DIWVGRIVIPHMLO-UHFFFAOYSA-M 0.000 description 4
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- CBOKAZFQZOQTOC-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]benzaldehyde Chemical compound CN(C)CCOC1=CC=C(C=O)C=C1 CBOKAZFQZOQTOC-UHFFFAOYSA-N 0.000 description 4
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- BHYVHYPBRYOMGC-UHFFFAOYSA-N ethyl 4-formylbenzoate Chemical compound CCOC(=O)C1=CC=C(C=O)C=C1 BHYVHYPBRYOMGC-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 208000017520 skin disease Diseases 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- QPFBLWIPCIVZOK-UHFFFAOYSA-N 1,3-bis(3,3-dimethyl-2,4-dihydro-1,5-benzodioxepin-7-yl)propan-2-one Chemical compound CC1(COC2=C(OC1)C=CC(=C2)CC(=O)CC1=CC2=C(OCC(CO2)(C)C)C=C1)C QPFBLWIPCIVZOK-UHFFFAOYSA-N 0.000 description 3
- SCWIEWRCUCQBFL-UHFFFAOYSA-N 1,3-bis(3,3-dimethyl-2,4-dihydro-1,5-benzodithiepin-7-yl)propan-2-one Chemical compound CC1(CSC2=C(SC1)C=CC(=C2)CC(=O)CC1=CC2=C(SCC(CS2)(C)C)C=C1)C SCWIEWRCUCQBFL-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HDMLSETVZQMXLU-UHFFFAOYSA-M 1-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethyl-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=C2SCCC(C)(C)C2=CC=1C(C)[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HDMLSETVZQMXLU-UHFFFAOYSA-M 0.000 description 3
- NMPKBMGUNSPVAA-UHFFFAOYSA-N 3,3-dimethyl-2,4-dihydro-1,5-benzodithiepine Chemical compound S1CC(C)(C)CSC2=CC=CC=C21 NMPKBMGUNSPVAA-UHFFFAOYSA-N 0.000 description 3
- CZNUTOFQWQZYQP-UHFFFAOYSA-N 4,4-dimethyl-6-(1-phenylprop-1-en-2-yl)-2,3-dihydrothiochromene Chemical compound C=1C=C2SCCC(C)(C)C2=CC=1C(C)=CC1=CC=CC=C1 CZNUTOFQWQZYQP-UHFFFAOYSA-N 0.000 description 3
- KIUXWPLBPPILPB-UHFFFAOYSA-N 4-[(4,4-dimethyl-2,3-dihydrothiochromene-7-carbonyl)amino]benzoic acid Chemical compound C=1C=C2C(C)(C)CCSC2=CC=1C(=O)NC1=CC=C(C(O)=O)C=C1 KIUXWPLBPPILPB-UHFFFAOYSA-N 0.000 description 3
- WERLNVNISGJFNF-UHFFFAOYSA-N 4-[(5-methyl-2,3,4,5-tetrahydro-1-benzothiepine-8-carbonyl)amino]benzoic acid Chemical compound C=1C=C2C(C)CCCSC2=CC=1C(=O)NC1=CC=C(C(O)=O)C=C1 WERLNVNISGJFNF-UHFFFAOYSA-N 0.000 description 3
- QNLKNFSEQSCQRR-UHFFFAOYSA-N 8-bromo-3,4-dihydro-2h-1-benzothiepin-5-one Chemical compound S1CCCC(=O)C=2C1=CC(Br)=CC=2 QNLKNFSEQSCQRR-UHFFFAOYSA-N 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- 238000003747 Grignard reaction Methods 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 238000007239 Wittig reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- XUQKRSKXICZLIX-UHFFFAOYSA-N ethyl 4-(2,3,4,5-tetrahydro-1-benzothiepine-8-carbonylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)C1=CC=C(CCCCS2)C2=C1 XUQKRSKXICZLIX-UHFFFAOYSA-N 0.000 description 3
- NCQKVYBKINERBK-UHFFFAOYSA-N ethyl 4-[2-(4,4-dimethyl-2,3-dihydrothiochromen-7-yl)prop-1-enyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C=C(C)C1=CC=C2C(C)(C)CCSC2=C1 NCQKVYBKINERBK-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
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- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
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- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
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- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
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- C—CHEMISTRY; METALLURGY
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- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- C07—ORGANIC CHEMISTRY
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2694/88-9 | 1988-07-14 | ||
| CH269488 | 1988-07-14 | ||
| CH1994/89-1 | 1989-05-26 | ||
| CH199489 | 1989-05-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0276862A JPH0276862A (ja) | 1990-03-16 |
| JPH0786094B2 true JPH0786094B2 (ja) | 1995-09-20 |
Family
ID=25689211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1181650A Expired - Lifetime JPH0786094B2 (ja) | 1988-07-14 | 1989-07-13 | 複素環式化合物 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US5037825A (de) |
| EP (1) | EP0350846B1 (de) |
| JP (1) | JPH0786094B2 (de) |
| KR (1) | KR900001672A (de) |
| AT (1) | ATE128974T1 (de) |
| AU (1) | AU626881B2 (de) |
| CA (1) | CA1319364C (de) |
| DE (1) | DE58909463D1 (de) |
| DK (1) | DK348189A (de) |
| ES (1) | ES2078905T3 (de) |
| FI (1) | FI96204C (de) |
| GR (1) | GR3018541T3 (de) |
| HU (1) | HU205084B (de) |
| IE (1) | IE70450B1 (de) |
| IL (1) | IL90912A (de) |
| MC (1) | MC2051A1 (de) |
| NO (1) | NO172644C (de) |
| NZ (1) | NZ229832A (de) |
| PT (1) | PT91158B (de) |
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| JP6051660B2 (ja) * | 2012-07-31 | 2016-12-27 | ユーハ味覚糖株式会社 | 新規レスベラトロール誘導体 |
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| US3635941A (en) * | 1969-04-01 | 1972-01-18 | Eastman Kodak Co | Disperse mono azo dyes containing an acylamidotetrahydroquinoline group |
| DE2260118C2 (de) * | 1972-12-08 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | Penicilline sowie ihre Verwendung als Arzneimittel |
| EP0086259A3 (de) * | 1981-11-13 | 1985-06-12 | Hamilton Bonaduz AG | Verfahren und Vorrichtung zur Bestimmung eines Gasdurchflusses |
| CH651034A5 (de) * | 1982-05-12 | 1985-08-30 | Hoffmann La Roche | Chroman-, thiochroman- oder 1,2,3,4-tetrahydrochinolinderivate und ihre verwendung als arzneimittel-wirkstoffe. |
| US4808597A (en) * | 1983-07-05 | 1989-02-28 | Pfizer Inc. | Method for inhibiting the degradation of cartilage |
| ATE38835T1 (de) * | 1983-07-05 | 1988-12-15 | Pfizer | Karbonsaeure-derivate verwendbar bei der verhuetung der zersetzung von knorpeln. |
| EP0155940A1 (de) * | 1983-08-08 | 1985-10-02 | Sri International | Benzonorbornenyl, benzopyranyl und benzothiopyranyl retinsäure analogen |
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| JPS6253981A (ja) * | 1985-09-02 | 1987-03-09 | Koichi Shiyudo | 新規安息香酸誘導体 |
| US4761424A (en) * | 1985-10-01 | 1988-08-02 | Warner-Lambert Company | Enolamides, pharmaceutical compositions and methods for treating inflammation |
| LU86259A1 (fr) * | 1986-01-21 | 1987-09-03 | Rech Dermatologiques C I R D S | Amides aromatiques,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| FR2618437B1 (fr) * | 1987-07-23 | 1989-11-17 | Rhone Poulenc Sante | Nouveaux derives du benzopyranne, leur preparation et les medicaments qui les contiennent |
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1989
- 1989-06-27 AU AU37097/89A patent/AU626881B2/en not_active Ceased
- 1989-07-05 NZ NZ229832A patent/NZ229832A/xx unknown
- 1989-07-10 CA CA000605266A patent/CA1319364C/en not_active Expired - Fee Related
- 1989-07-10 US US07/377,510 patent/US5037825A/en not_active Expired - Fee Related
- 1989-07-10 ES ES89112607T patent/ES2078905T3/es not_active Expired - Lifetime
- 1989-07-10 AT AT89112607T patent/ATE128974T1/de active
- 1989-07-10 DE DE58909463T patent/DE58909463D1/de not_active Expired - Fee Related
- 1989-07-10 IL IL9091289A patent/IL90912A/en not_active IP Right Cessation
- 1989-07-10 EP EP89112607A patent/EP0350846B1/de not_active Expired - Lifetime
- 1989-07-10 HU HU893454A patent/HU205084B/hu not_active IP Right Cessation
- 1989-07-13 MC MC892064A patent/MC2051A1/fr unknown
- 1989-07-13 IE IE227289A patent/IE70450B1/en not_active IP Right Cessation
- 1989-07-13 PT PT91158A patent/PT91158B/pt not_active IP Right Cessation
- 1989-07-13 NO NO892894A patent/NO172644C/no unknown
- 1989-07-13 KR KR1019890009946A patent/KR900001672A/ko not_active Ceased
- 1989-07-13 JP JP1181650A patent/JPH0786094B2/ja not_active Expired - Lifetime
- 1989-07-13 DK DK348189A patent/DK348189A/da not_active Application Discontinuation
- 1989-07-14 FI FI893433A patent/FI96204C/fi not_active IP Right Cessation
-
1992
- 1992-08-18 US US07/931,612 patent/US5300522A/en not_active Expired - Fee Related
-
1993
- 1993-12-23 US US08/173,796 patent/US5420273A/en not_active Expired - Fee Related
-
1995
- 1995-12-27 GR GR950403684T patent/GR3018541T3/el unknown
Non-Patent Citations (1)
| Title |
|---|
| J.Chem.Eng.Data.第21巻第1号第125−131頁(1976) |
Also Published As
| Publication number | Publication date |
|---|---|
| IL90912A0 (en) | 1990-02-09 |
| IE892272L (en) | 1990-01-14 |
| NO172644B (no) | 1993-05-10 |
| JPH0276862A (ja) | 1990-03-16 |
| NO172644C (no) | 1993-08-18 |
| FI96204B (fi) | 1996-02-15 |
| NZ229832A (en) | 1992-08-26 |
| CA1319364C (en) | 1993-06-22 |
| DK348189D0 (da) | 1989-07-13 |
| AU626881B2 (en) | 1992-08-13 |
| HUT50786A (en) | 1990-03-28 |
| DK348189A (da) | 1990-01-15 |
| NO892894D0 (no) | 1989-07-13 |
| FI96204C (fi) | 1996-05-27 |
| EP0350846A2 (de) | 1990-01-17 |
| US5300522A (en) | 1994-04-05 |
| IL90912A (en) | 1994-01-25 |
| FI893433A0 (fi) | 1989-07-14 |
| ATE128974T1 (de) | 1995-10-15 |
| MC2051A1 (fr) | 1990-07-17 |
| AU3709789A (en) | 1990-01-18 |
| NO892894L (no) | 1990-01-15 |
| GR3018541T3 (en) | 1996-03-31 |
| FI893433A7 (fi) | 1990-01-15 |
| HU205084B (en) | 1992-03-30 |
| US5037825A (en) | 1991-08-06 |
| IE70450B1 (en) | 1996-11-27 |
| ES2078905T3 (es) | 1996-01-01 |
| EP0350846A3 (en) | 1990-11-07 |
| KR900001672A (ko) | 1990-02-27 |
| DE58909463D1 (de) | 1995-11-16 |
| US5420273A (en) | 1995-05-30 |
| EP0350846B1 (de) | 1995-10-11 |
| PT91158A (pt) | 1990-02-08 |
| PT91158B (pt) | 1995-03-01 |
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